US9410016B2 - Aromatic polyacetals and articles comprising them - Google Patents

Aromatic polyacetals and articles comprising them Download PDF

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US9410016B2
US9410016B2 US13/943,169 US201313943169A US9410016B2 US 9410016 B2 US9410016 B2 US 9410016B2 US 201313943169 A US201313943169 A US 201313943169A US 9410016 B2 US9410016 B2 US 9410016B2
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hydrogen
substituted
unsubstituted
hydroxyl
ochve
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US20150025278A1 (en
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Matthias S. Ober
Duane R. Romer
John B. Etienne
Pulikkottil J. Thomas
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Dow Chemical Co
DDP Specialty Electronic Materials US LLC
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Dow Global Technologies LLC
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Priority to JP2014144250A priority patent/JP5813832B2/ja
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Priority to TW103124362A priority patent/TWI554553B/zh
Priority to KR1020140090030A priority patent/KR101618179B1/ko
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    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
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    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/312—Non-condensed aromatic systems, e.g. benzene
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    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
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    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
    • C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
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    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/344—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing heteroatoms
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    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
    • C08G2650/12—Depolymerisation, e.g. to reform the monomer

Definitions

  • the present invention relates to polymers, in particular aromatic polyacetals and polyketals.
  • Poly(methacrylate)-based and poly(hydroxystyrene)-based chemically amplified photoresists have reached a performance limit that is defined by a trade-off triangle of resolution, line edge roughness, and sensitivity. This is the so-called RLS trade-off.
  • RLS trade-off There is empirical evidence that attempts to increase one of the key properties by using a formulation approach hurt the remaining properties of the triangle. This effect limits the achievable feature size in high resolution photolithography, including extreme ultraviolet (EUV) and electron beam.
  • EUV extreme ultraviolet
  • One way to escape the RLS trade-off triangle of poly(methacrylate)-based and poly(hydroxystyrene)-based chemically amplified photoresists would be to create new photoresist compositions based on a different polymer that provides one or more of improved photon absorption, improved quantum efficiency, and improved efficiency of a catalytic chain reaction.
  • An additional way to escape the RLS trade-off triangle of poly(methacrylate)-based and poly(hydroxystyrene)-based chemically amplified photoresists would be to create new photoresist compositions based on a different polymer that exhibits non-constant diffusion behavior (i.e., the diffusion constant of the acid is higher in the exposed area than the unexposed area) during photolithography.
  • each occurrence of R 1 and R 2 is independently hydrogen, unsubstituted or substituted C 1-18 linear or branched alkyl, unsubstituted or substituted C 3-18 cycloalkyl, unsubstituted or substituted C 6-18 aryl, or unsubstituted or substituted C 3-18 heteroaryl; and R 1 and R 2 are optionally covalently linked to each other to form a ring that includes —R 1 —C—R 2 —, where the central carbon is the acetal carbon; each occurrence of Ar 1 , Ar 2 , and Ar 3 is independently unsubstituted or substituted C 6-18 arylene, or unsubstituted or substituted C 3-18 heteroarylene; provided that at least one occurrence of Ar 1 , Ar 2 , and Ar 3 is substituted with at least one functional group selected from hydroxyl, acetal, ketal, ester, and lactone.
  • Another embodiment is an article comprising the polymer.
  • FIG. 1 shows polymer backbone and side chain degradation of the polymer pBEBA-2,4-DBP-CHVE from Example 8 after treatment with dilute aqueous triflic acid.
  • FIG. 2 shows that acid treatment of the polymer significantly affects its solubility properties.
  • the present inventors have prepared polymers containing labile acetal groups within the polymer backbone, and, optionally, additional labile functional groups pendant to the polymer. Under acidic conditions, depolymerization and deprotection of any acid-sensitive protecting groups is achieved simultaneously.
  • the polymers therefore provide improved efficiency of the catalytic chain reaction relative to poly(methacrylate)s and poly(hydroxystyrene)s.
  • the polymers can exhibit other properties that make them particularly useful for lithography.
  • These properties can include one or more of high glass transition temperature, high ring parameter, low Ohnishi parameter (improved etch resistance), solubility in solvents common for photoresist formulations, heat stability of the polymer backbone, and solubility in aqueous basic developer after depolymerization and deprotection.
  • acetal shall be understood to be generic to “acetal” and “ketal”
  • oligoacetal shall be understood to be generic to “oligoacetal” and “oligoketal”
  • polyacetal shall be understood to be generic to “polyacetal” and “polyketal”.
  • the term “plurality” means at least three.
  • the term “polymer” will be understood to encompass oligomers comprising as few as three repeat units. The desired number of repeat units will depend on the intended use of the polymer.
  • the polymer when used in a photoresist composition, it may be desirable for the polymer to comprise at least 5 repeat units, specifically 5 to 200 repeat units.
  • substituted means including at least one substituent such as a halogen (i.e., F, Cl, Br, I), hydroxyl, amino, thiol, carboxyl, carboxylate, amide, nitrile, sulfide, disulfide, nitro, C 1-18 alkyl, C 1-18 alkoxyl, C 6-18 aryl, C 6-18 aryloxyl, C 7-18 alkylaryl, or C 7-18 alkylaryloxyl.
  • halogen i.e., F, Cl, Br, I
  • hydroxyl amino, thiol
  • carboxyl carboxyl
  • carboxylate amide
  • nitrile sulfide
  • disulfide disulfide
  • fluorinated means having one or more fluorine atoms incorporated into the group.
  • the fluoroalkyl group can include one or more fluorine atoms, for example, a single fluorine atom, two fluorine atoms (e.g., as a 1,1-difluoroethyl group), three fluorine atoms (e.g., as a 2,2,2-trifluoroethyl group), or fluorine atoms at each free valence of carbon (e.g., as a perfluorinated group such as —CF 3 , —C 2 F 5 , —C 3 F 7 , or —C 4 F 9 ).
  • a perfluorinated group such as —CF 3 , —C 2 F 5 , —C 3 F 7 , or —C 4 F 9 ).
  • each occurrence of R 1 and R 2 is independently hydrogen, unsubstituted or substituted C 1-18 linear or branched alkyl, unsubstituted or substituted C 3-18 cycloalkyl, unsubstituted or substituted C 6-18 aryl, or unsubstituted or substituted C 3-18 heteroaryl; and R 1 and R 2 are optionally covalently linked to each other to form a ring that includes —R 1 —C—R 2 —, where the central carbon is the acetal carbon; each occurrence of Ar 1 , Ar 2 , and Ar 3 is independently unsubstituted or substituted C 6-18 arylene, or unsubstituted or substituted C 3-18 heteroarylene; provided that at least one functional group selected from hydroxyl, acetal, ketal, ester, and lactone.
  • the polymer comprises a plurality of repeat units having the structure
  • the repeat units can be formed by Suzuki polycondensation of one or more bis(aryl)acetal compounds having the structure
  • B x is a boron-containing functional group bonded to Ar 1 via a boron atom; Y is chloro, bromo, iodo, triflate, mesylate, or tosylate; and R 1 , R 2 , Ar 1 , and Ar 2 are defined above.
  • B x groups include —BF 3 ⁇ M + , wherein each occurrence of M + is independently an alkali metal cation, or an unsubstituted or substituted ammonium ion; —B(OH) 2 ; and
  • R 3 and R 4 are each independently C 1-18 alkyl, C 3-18 cycloalkyl, or C 6-18 aryl; and R 3 and R 4 are optionally covalently linked to each other to form a ring that includes —R 3 —O—B—O—R 4 —.
  • the first method comprises Suzuki polycondensation of a bis(aryl)acetal compound having the structure
  • B x , R 1 , R 2 , Ar 1 , and Ar 2 are defined above and each occurrence of B x is defined independently, with a bis(leaving group)arylene having the structure Y—Ar 3 —Y wherein Y and Ar 3 are defined above, and each occurrence of Y is defined independently.
  • the second method comprises Suzuki polycondensation of a bis(aryl)acetal compound having the structure
  • Y, R 1 , R 2 , Ar 1 , and Ar 2 are defined above and each occurrence of Y is defined independently, with a bis(leaving group)arylene having the structure B x —Ar 3 —B x wherein B x and Ar 3 are defined above and each occurrence of B x is defined independently.
  • R 14 is independently unsubstituted or substituted C 1-18 linear or branched alkyl, unsubstituted or substituted C 3-18 cycloalkyl, unsubstituted or substituted C 6-18 aryl, or unsubstituted or substituted ferrocenyl;
  • R 15 , R 16 , R 17 , R 18 , R 19 are, independently, hydrogen, C 1-6 linear or branched alkyl, C 3-6 cycloalkyl, or phenyl; and Z is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano (—CN), cyanate (—OCN), isocyanate (—NCO), thiocyanate (—SCN), isothiocyanate (—NCS), nitro (—NO 2 ), nitrite (—ON ⁇ O), azide (—N ⁇ N + ⁇ N ⁇ ), and hydroxyl.
  • One advantage of the present polymers is that the Suzuki polycondensation used in their preparation tolerates functional groups that would be incompatible with a polyacetal synthesis in which the acetal-containing backbone is formed in the last step. Specifically, at least one occurrence of Ar 1 , Ar 2 , and Ar 3 (when present) is substituted with at least one functional group selected from hydroxyl, acetal, ketal, ester, and lactone.
  • the acetals can be monovalent acetals having the structure —O—C(H)(R 5 )—OR 6 , wherein R 5 and R 6 are independently selected from the group consisting of unsubstituted or substituted C 1-18 linear or branched alkyl, unsubstituted or substituted C 3-18 cycloalkyl, unsubstituted or substituted C 6-18 aryl, and unsubstituted or substituted C 3-18 heteroaryl; optionally R 5 or R 6 is covalently connected to the polymer backbone (e.g., via bonding to R 1 or R 2 , or to one of Ar 1 , Ar 2 , and Ar 3 to which the oxygen end of the acetal is not already bound).
  • R 5 and R 6 are independently selected from the group consisting of unsubstituted or substituted C 1-18 linear or branched alkyl, unsubstituted or substituted C 3-18 cycloalkyl, unsubstituted or substituted C
  • the acetal is part of a ring structure.
  • the ring structure can include or not include Ar 1 —O—C—O—Ar 2 .
  • R 5 and R 6 are covalently connected to each others to form a ring structure.
  • Specific examples of monovalent acetals having the structure —O—C(H)(R 5 )—OR 6 include
  • the acetals can also be divalent cyclic acetals attached via oxygen atoms to Ar 1 , Ar 2 , or Ar 3 as shown in the structure
  • Ar n is Ar 1 , Ar 2 , or Ar 3 (when present), or a combination of Ar 1 and Ar 2 (for example, when one acetal oxygen is bonded directly to Ar 1 and the other directly to Ar 2 ) or a combination of Ar 2 and Ar 3 ;
  • R 10 is selected from the group consisting of unsubstituted or substituted C 1-18 linear or branched alkyl, unsubstituted or substituted C 3-18 cycloalkyl, unsubstituted or substituted C 6-18 aryl, and unsubstituted or substituted C 3-18 heteroaryl.
  • the cyclic acetal is part of a ring structure that includes Ar 1 —O—C(R 1 )(R 2 )—O—Ar 2 . In other embodiments, the cyclic acetal is not part of such a ring structure.
  • the ketals can be monovalent ketals having the structure —O—C(R 7 )(R 8 )—OR 9 , wherein R 7 , R 8 , and R 9 are independently selected from the group consisting of unsubstituted or substituted C 1-18 linear or branched alkyl, unsubstituted or substituted C 3-18 cycloalkyl, unsubstituted or substituted C 6-18 aryl, and unsubstituted or substituted C 3-18 heteroaryl.
  • R 7 , R 8 , or R 9 is covalently connected to the polymer backbone such that the acetal is part of a ring structure.
  • the ketals can also be cyclic ketals attached via oxygen atoms to Ar 1 or Ar 2 as shown in the structure
  • Ar n is Ar 1 or Ar 2 , or a combination of Ar 1 and Ar 2 (for example, when one ketal oxygen is bonded directly to Ar 1 and the other directly to Ar 2 );
  • R 11 and R 12 are independently selected from the group consisting of unsubstituted or substituted C 1-18 linear or branched alkyl, unsubstituted or substituted C 3-18 cycloalkyl, unsubstituted or substituted C 6-18 aryl, and unsubstituted or substituted C 3-18 heteroaryl.
  • the cyclic ketal is part of a ring structure that includes Ar 1 —O—C(R 1 )(R 2 )—O—Ar 2 . In other embodiments, the cyclic ketal is not part of such a ring structure.
  • the esters can have the structure —(O) a -(L 1 ) b -C( ⁇ O)—OR 13 , wherein a is 0 or 1 and b is 0 or 1, provided that when a is 1 then b is 1; R 13 is selected from the group consisting of unsubstituted or substituted C 1-20 linear or branched alkyl (e.g., methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, diphenylmethyl, 2-phenylpropan-2-yl, 1,1-diphenylethan-1-yl, triphenylmethyl), unsubstituted or substituted C 3-20 cycloalkyl (e.g., cyclopentyl, cyclohexyl, methylcyclohexan-1-yl, ethylcyclohexan-1-yl, 1-norbornyl,
  • the esters can have the structure —(O) c -(L 2 ) d -O—C( ⁇ O)—R 14 , wherein c is 0 or 1 and d is 0 or 1, provided that when c is 1 then d is 1; R 14 is selected from the group consisting of unsubstituted or substituted C 1-20 linear or branched alkyl (e.g., methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, diphenylmethyl, 2-phenylpropan-2-yl, 1,1-diphenylethan-1-yl, and triphenylmethyl), unsubstituted or substituted C 3-20 cycloalkyl (e.g., cyclopentyl, cyclohexyl, 1-norbornyl, 1-adamantlyl, 2-methylbicyclo[2.2.1]heptan-2-y
  • R 14 and L 2 are covalently connected to each others to form a lactone.
  • a specific example of an ester having the structure —(O) c -(L 2 ) d -O—C( ⁇ O)—R 14 is
  • the lactones can have the structure
  • R 50 is hydrogen, unsubstituted or substituted C 1-18 linear or branched alkyl, unsubstituted or substituted C 3-18 cycloalkyl, unsubstituted or substituted C 6-18 aryl, or unsubstituted or substituted C 3-18 heteroaryl; and L 3 is selected from the group consisting of unsubstituted or substituted C 1-20 linear or branched alkylene (e.g., unsubstituted or substituted C 3-20 cycloalkylene (e.g., 1,1-cyclopentanediyl, 1,2-cyclopentanediyl, 1,1-cyclohexanediyl, 1,4-cyclohexanediyl), unsubstituted or substituted C 6-20 arylene (e.g., 1,3-phenylene, 1,4-phen
  • At least one of Ar 1 , Ar 2 and Ar 3 is substituted with at least one hydroxyl.
  • the mole percent of repeat units in which at least one of Ar 1 , Ar 2 and Ar 3 is substituted with at least one hydroxyl can be at least 70 mole percent, at least 90 mole percent, at least 95 mole percent, at least 98 mole percent, or at least 99 mole percent.
  • At least one of R 1 , R 2 , Ar 1 , Ar 2 and Ar 3 is substituted with hydroxyl. In some embodiments, at least one of R 1 , R 2 , Ar 1 , Ar 2 , and Ar 3 (when present) is substituted with hydroxyl in at least 40 mole percent of the plurality of repeat units. In some embodiments, in 40 to 99 mole percent of the plurality of repeat units at least one of Ar 1 , Ar 2 , and Ar 3 (when present) is substituted with hydroxyl, and in 1 to 60 mole percent of the plurality of repeat units at least one of Ar 1 , Ar 2 and Ar 3 is substituted with the acetal or ketal.
  • a preferred acetal is —O—C(H)(R 5 )—OR 6 , wherein R 5 is methyl and R 6 is cyclohexyl.
  • each occurrence of Ar 1 , Ar 2 , and Ar 3 is independently 1,3-phenylene or 1,4-phenylene.
  • Ar 1 and Ar 2 are not covalently linked with one another via an acid-robust linkage to form a ring structure that includes —Ar 1 —O—C—O—Ar 2 —.
  • Ar 1 , Ar 2 , and Ar 3 include unsubstituted or substituted 1,2-phenylene, unsubstituted or substituted 1,3-phenylene, unsubstituted or substituted 1,4-phenylene, unsubstituted or substituted 4,4′-biphenylene, unsubstituted or substituted 4,4′′-p-terphenylene, unsubstituted or substituted 3,3′′-p-terphenylene, unsubstituted or substituted 4,4′′-m-terphenylene, unsubstituted or substituted 4,4′′-p-terphenylene, unsubstituted or substituted 4,4′′-o-terphenylene, unsubstituted or substituted 2,2′′-o-terphenylene, unsubstituted or substituted 1,4-naphthylene, unsubstituted or substituted 2,7-naphthylene, unsubstituted or substituted 2,6-na
  • Ar 1 and Ar 2 are covalently linked with one another via the —O—C—O— linkage of the acetal.
  • Ar 1 and Ar 2 are not further covalently linked with one another to form a ring structure that includes —Ar 1 —O—C—O—Ar 2 —.
  • Ar 1 and Ar 2 are covalently linked only via the —O—C—O— linkage of the acetal.
  • R 1 and R 2 are each independently hydrogen, unsubstituted or substituted C 1-18 linear or branched alkyl (e.g., methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 1methyl-2-propyl, diphenylmethyl, 2-phenylpropan-2-yl, 1,1-diphenylethan-1-yl, and triphenylmethyl), unsubstituted or substituted C 3-20 cycloalkyl (e.g., cyclopentyl, cyclohexyl, 1-norbornyl, 1-adamantlyl, 2-methylbicyclo[2.2.1]heptan-2-yl, 2-methyladamantan-2-yl); unsubstituted or substituted C 6-18 aryl (e.g., phenyl, 1-naphthyl, 2-naphthyl, anthracenyl), or unsubstituted C 1-18 linear or
  • R 1 and R 2 are hydrogen or methyl.
  • R 1 is hydrogen
  • R 2 is selected from phenyl, ortho-methoxyphenyl, meta-methoxyphenyl, and para-methoxyphenyl.
  • R 1 is hydrogen and R 2 is unsubstituted or substituted phenyl.
  • R 2 is substituted phenyl, it can be substituted with a hydroxyl group, an acetal group, an ester group (including a lactone), or other such group that would be incompatible with polyacetal formation via acetal-generating polycondensation or would cause undesired polymer crosslinking.
  • the polymer is end-capped with terminal groups —Ar 4 , wherein each Ar 4 is independently an unsubstituted or substituted C 6-18 arylene, or unsubstituted or substituted C 3-18 heteroarylene.
  • Ar 4 include
  • At least one endcapping reagent of the form Ar 4 —X or Ar 4 —B x , wherein X and B x are defined above, is added after completion of the polymerization reaction as a method to (1) reduce the halogen and/or boron content of the polymer and/or (2) to adjust polymer properties that include solubility and substrate adhesion.
  • a suitable amount of endcapping reagent is 0.01 to 5 equivalents with respect to the initial monomer concentration, specifically 0.1 to 0.3 equivalents with respect to the initial monomer concentration.
  • At least one endcapping reagent of the form Ar 4 —X or Ar 4 —B x , wherein X and B x are defined above, is added at the beginning or during the course of the polymerization as a method to (1) limit molecular weight, (2) reduce the halogen and/or boron content of the final polymer and/or (3) to adjust specific polymer properties that include solubility and substrate adhesion.
  • the polymer comprises a plurality of repeat units having the structure
  • R 21 is hydroxyl and the other three occurrence of R 21 are hydrogen; or two occurrences of R 21 are hydroxyl and the other two occurrences of R 21 are hydrogen; or three occurrences of R 21 are hydroxyl and the other occurrence of R 21 is hydrogen; or all four occurrences of R 21 are hydroxyl; or any of the foregoing occurrences of R 21 that are hydroxyl can instead be an acetal or an ester;
  • R 21 is hydroxyl and the other three occurrence of R 21 are hydrogen; or two occurrences of R 21 are hydroxyl and the other two occurrences of R 21 are hydrogen; or three occurrences of R 21 are hydroxyl and the other occurrence of R 21 is hydrogen; or all four occurrences of R 21 are hydroxyl; or any of the foregoing occurrences of R 21 that are hydroxyl can instead be an acetal or an ester; in some embodiments, the polymer comprises a plurality of repeat units selected from
  • R 101 is hydrogen or hydroxyl, and R 102 is hydroxyl when R 101 is hydrogen, or R 102 is hydrogen when R 101 is hydroxyl;
  • R 201 is hydrogen or —OCHVE
  • R 202 is —OCHVE when R 201 is hydrogen, or hydrogen when R 201 is —OCHVE, wherein —OCHVE is
  • R 301 is —O—C( ⁇ O)—CH 3 (acetate) or —OCHVE
  • R 302 is —OCHVE when R 301 is —OC( ⁇ O)—CH 3 (acetate), or —OC( ⁇ O)—CH 3 (acetate) when R 301 is —OCHVE;
  • R 401 and R 402 are each independently hydroxyl or —OCHVE;
  • R 501 is hydrogen or hydroxyl
  • R 502 is hydroxyl when R 501 is hydrogen, or R 502 is hydrogen when R 501 is hydroxyl;
  • R 601 is hydrogen or —OCHVE
  • R 602 is —OCHVE when R 601 is hydrogen, or hydrogen when R 601 is —OCHVE;
  • R 701 is hydrogen or hydroxyl, and R 702 is hydroxyl when R 701 is hydrogen, or R 702 is hydrogen when R 701 is hydroxyl;
  • R 801 is hydrogen or —OCHVE
  • R 802 is —OCHVE when R 801 is hydrogen, or hydrogen when R 801 is —OCHVE;
  • R 901 is hydrogen or hydroxyl
  • R 902 is hydroxyl when R 901 is hydrogen, or R 902 is hydrogen when R 901 is hydroxyl;
  • R 1001 is hydrogen or —OCHVE
  • R 1002 is —OCHVE when R 1001 is hydrogen, or hydrogen when R 1001 is —OCHVE;
  • R 1101 is hydrogen or O—CH 2 —C( ⁇ O)—O-Ad
  • R 1102 is —O—CH 2 —C( ⁇ O)—O-Ad when R 1101 is hydrogen, or hydrogen when R 1101 is —O—CH 2 —C( ⁇ O)—O-Ad, wherein —CH 2 —C( ⁇ O)—O-Ad is
  • polymers include a polymer comprising repeat units having the structure
  • R 101 is hydrogen or hydroxyl, and R 102 is hydroxyl when R 101 is hydrogen, or R 102 is hydrogen when R 101 is hydroxyl; a polymer comprising repeat units having the structure
  • R 101 is hydrogen or hydroxyl
  • R 102 is hydroxyl when R 101 is hydrogen, or R 102 is hydrogen when R 101 is hydroxyl (preferably in an amount of 60 to 99 mole percent of total repeat units), and repeat units having the structure
  • R 201 is hydrogen or —OCHVE
  • R 202 is —OCHVE when R 201 is hydrogen, or hydrogen when R 201 is —OCHVE, wherein —OCHVE is
  • R 301 is —O—C( ⁇ O)—CH 3 (acetate) or —OCHVE
  • R 302 is —OCHVE when R 301 is —OC( ⁇ O)—CH 3 (acetate), or —OC( ⁇ O)—CH 3 (acetate) when R 301 is —OCHVE
  • a polymer comprising repeat units having the structure
  • R 401 and R 402 are each independently hydroxyl or —OCHVE (preferably such that about 1 to about 70 mole percent of the total moles of R 401 and R 402 are —OCHVE, and 60 to 99 mole percent of the total moles of R 401 and R 402 are hydroxyl); a polymer comprising repeat units having the structure
  • R 501 is hydrogen or hydroxyl
  • R 502 is hydroxyl when R 501 is hydrogen, or R 502 is hydrogen when R 501 is hydroxyl (preferably in an amount of 60 to 99 mole percent of total repeat units), and repeat units having the structure
  • R 601 is hydrogen or —OCHVE
  • R 602 is —OCHVE when R 601 is hydrogen, or hydrogen when R 601 is —OCHVE (preferably in an amount of 1 to 40 mole percent of total repeat units); a polymer comprising repeat units having the structure
  • R 701 is hydrogen or hydroxyl
  • R 702 is hydroxyl when R 701 is hydrogen, or R 702 is hydrogen when R 701 is hydroxyl (preferably in an amount of 60 to 99 mole percent of total repeat units), and repeat units having the structure
  • R 801 is hydrogen or —OCHVE
  • R 802 is —OCHVE when R 801 is hydrogen, or hydrogen when R 801 is —OCHVE (preferably in an amount of 1 to 40 mole percent of total repeat units); a polymer comprising repeat units having the structure
  • R 901 is hydrogen or hydroxyl
  • R 902 is hydroxyl when R 901 is hydrogen, or R 902 is hydrogen when R 901 is hydroxyl (preferably in an amount of 60 to 99 mole percent of total repeat units), and repeat units having the structure
  • R 1001 is hydrogen or —OCHVE
  • R 1002 is —OCHVE when R 1001 is hydrogen, or hydrogen when R 1001 is —OCHVE (preferably in an amount of 1 to 40 mole percent of total repeat units); a polymer comprising repeat units having the structure
  • R 1101 is hydrogen or O—CH 2 —C( ⁇ O)—O-Ad
  • R 1102 is —O—CH 2 —C( ⁇ O)—O-Ad when R 1101 is hydrogen, or hydrogen when R 1101 is —O—CH 2 —C( ⁇ O)—O-Ad, wherein —CH 2 —C( ⁇ O)—O-Ad is
  • the polymer comprises a plurality of repeat units having the structure
  • each occurrence of Ar 1 and Ar 2 is 1,4-phenylene; each occurrence of Ar 3 is unsubstituted or substituted 1,3-phenylene, wherein, in at least 40 mole percent of the plurality of repeat units, Ar 3 is substituted with at least one hydroxyl; each occurrence of R 1 is hydrogen; and each occurrence of R 2 is phenyl.
  • the polymer can be used in various articles and applications, including biological applications (e.g., pH-dependent delivery of active agents including pharmaceuticals), prodrugs and amplified drug release, microencapsulation and extended release applications (e.g., encapsulation of active agents for pharmaceutical or agricultural applications); diagnostic applications; signal amplification; photoresists for lithography, including lithography using ultraviolet (UV) wavelengths, extreme ultraviolet wavelengths (EUV), and electron beams, photoresist topcoats and underlayers; electronic devices including patternable light emitting devices (OLED/PLED), photovoltaic devices, organic thin-film transistors (TFTs), and molecular logic gates; photographic applications such as detection or imaging of radioactive compounds or UV radiation; and pH indicators.
  • biological applications e.g., pH-dependent delivery of active agents including pharmaceuticals
  • prodrugs and amplified drug release e.g., encapsulation of active agents for pharmaceutical or agricultural applications
  • diagnostic applications amplification
  • photoresists for lithography including lithography
  • Infrared spectra were acquired with a Perkin Elmer Spectrum One FT-IR and Universal ATR Sampling Accessory at a nominal resolution of 4 centimeter ⁇ 1 and 16 scans (approximate acquisition time of 90 seconds).
  • the Universal ATR Sampling Accessory was equipped with a single bounce diamond/ZnSe crystal.
  • T m and T g glass transition temperatures were determined by differential scanning calorimetry (DSC) using TA Instruments Q2000 DSC, using T4 calibration (Indium, Sapphire). Approximately 5 milligrams of each sample was weighed into a TZero Aluminum DSC pan with lid. A heat:cool:heat temperature profile at a ramp rate of 10° C./minute was used, under nitrogen purge. Samples were heated from room temperature to 150° C., cooled to ⁇ 90° C., and heated again to 150° C. Data analysis was performed using TA Universal Analysis software.
  • T d Thermal decomposition temperatures
  • the resulting oil was taken up in 50 milliliters hexanes and filtered through a plug of basic alumina. The plug was washed with 1.4 liters of a 1:1 solution of hexane and diethyl ether. The solvent was removed on the rotary evaporator and the resulting oil further dried under high vacuum for at least 24 hours. The product was obtained as a racemate in the form a colorless oil in a yield of 75% (9.35 grams, 24.7 millimoles).
  • FTIR thin film: 595, 641, 670, 689, 719, 782, 796, 817, 867, 891, 906, 959, 979, 1022, 1038, 1069, 1141, 1232, 1242, 1261, 1280, 1344, 1376, 1450, 1469, 1578, 2856, 2932, 2991 cm ⁇ 1 ; UV/Vis: 225 (shoulder), 238, 286 nm; HRMS (GC/MS/NCI—NH3): 374.95735 calc. for C 14 H 17 Br 2 O 2 [M-H] ⁇ , 374.9601, found 374.9591.
  • the resulting oil was taken up in hexanes (50 milliliters) and filtered through a plug of basic alumina, using additional hexane ( ⁇ 1 liter) to completely elute the product.
  • the solvent was removed on the rotary evaporator and the resulting product was further dried under high vacuum for at least 24 hours.
  • the target compound was obtained as a racemic mixture of diastereomers in the form of a slightly yellow oil (16.1 grams, 30.9 millimoles, 79%).
  • 1 H-NMR 400 MHz, CDCl 3 ) ⁇ 7.67 (s, 0.47H (diast. a)), 7.67 (s, 0.53H (diast.
  • the mixture was allowed to stir for 5 minutes, and the precipitate was removed by filtration.
  • the product was purified by gradient flash column chromatography (ethyl acetate in hexane, 0 to 40%). The product was obtained in the form of a colorless solid (6.73 grams, 21.7 millimoles, 55%).
  • the resulting oil was taken up in diethyl ether (30 milliliters) and filtered through a plug of basic alumina. The product was rinsed through with additional ether (500 milliliters). The solvent was removed on the rotary evaporator and the resulting oil was pumped on for over 24 hours. The product was obtained as a racemate in the form of a slightly yellow oil (3.77 grams, 8.64 millimoles, 67%).
  • the aqueous phase was extracted with a 1:1 mixture of diethyl ether and ethyl acetate (3 ⁇ 120 mL). The combined organic phases were then washed with de-ionized water (5 ⁇ 100 milliliters), brine (1 ⁇ 100 milliliters) and dried over magnesium sulfate. After filtration and concentration on the rotary evaporator, the residue was taken up in diethyl ether (60 milliliters) and filtered through a plug of basic alumina. The product was fully eluted with additional diethyl ether (700 milliliters) and concentrated on the rotary evaporator.
  • diboronic acid ester 7.0 grams, 13.25 millimoles, 1.00 equivalent
  • [1-(cyclohexyloxy)ethoxy]-2,5 dibromophenol 4.81 grams, 12.72 millimoles, 0.96 equivalent
  • oxygen free 1,4-dioxane 60 milliliters
  • This example illustrates synthesis of partially protected poly(arylacetal) polymer using mixed polymerization with a phenol-tolerant Suzuki coupling catalyst.
  • 2,2′-(((phenylmethylene)bis(oxy))bis(4,1-phenylene))-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (8.000 grams, 15.14 millimoles, 1.000 equivalent) and 2,4-dibromo-1-(1-(cyclohexyloxy)ethoxy)benzene (1.632 grams, 4.316 millimoles, 0.285 equivalent) were combined in a round bottom flask.
  • potassium phosphate (10.06 grams, 47.4 millimoles, 3.13 equivalents) were dissolved in deoxygenated water (13 milliliters).
  • Pd(crotyl)(P-tBu 3 )Cl 6.0 milligrams, 15 micromoles, 0.001 equivalent
  • 1,4-dioxane 50 milliliters was added to the main reaction vessel followed by the potassium phosphate solution. The mixture was vigorously stirred, until an emulsion was formed. The catalyst solution was then added via cannula.
  • the aqueous layer was removed and the remaining organic phase was further washed with brine (1 ⁇ 50 milliliters).
  • the organic phase was transferred into a round bottom flask equipped with reflux condenser, a saturated aqueous solution of sodium diethyldithiodicarbamate ( ⁇ 10 milliliters) was added, and the mixture was vigorously stirred under reflux for 60 minutes.
  • the organics phase was separated, dried over magnesium sulfate and filtered through a three-layered plug of CELITETM diatomaceous earth ( ⁇ 0.25 inch on top), FLORISILTM activated magnesium silicate (0.15 inch in middle), and silica gel (0.15 inch on bottom).
  • the crude product was fully eluted with 200 milliliters ethyl acetate and the combined organic phases were washed with deionized water (5 ⁇ 50 milliliters) and concentrated on the rotary evaporator. The residue was taken up in ethyl acetate ( ⁇ 50 milliliters) with toluene (5-10 milliliters). The polymer was precipitated by drop-wise addition to stirred methanol (700 milliliters). Once the addition was complete, the suspension was stirred for 30 minutes and then allowed to settle. The precipitate was collected by filtering through a pre-washed disposable filter cartridge and air dried.
  • FIG. 1 shows polymer backbone and side chain degradation of the polymer pBEBA-2,4-DBP-CHVE from Preparative Example 8 after treatment with dilute aqueous triflic acid.
  • one equivalent of acetaldehyde is formed that can be monitored by integration of a diagnostic aldehyde proton via 1 H-NMR (upper curve).
  • Backbone degradation results in formation of one equivalent of benzaldehyde per degraded acetal unit and can be monitored by integration of the diagnostic benzaldehyde proton via 1 H-NMR (lower curve).
  • Backbone and side-chain degradation are two independent processes that occur at different rates. Acid sensitivity of backbone acetals and side chain acetals can be independently adjusted by selecting appropriate substitutions patterns on the respective acetals.
  • FIG. 2 shows that acid treatment significantly affects the solubility properties of the polymer systems disclosed herein, using pBEBA-2,4-DBP-CHVE (Preparative Example 8) as an example substrate.
  • vial (3) 2.5 milligrams of pBEBA-2,4-DBP-CHVE (4.8 kDa) was dissolved in 100 microliters of THF. The vial was further treated with approximately 50 microliters of concentrated trifluoroacetic acid, upon which the content of the vial turned red.
  • TMAH tetramethylammonium hydroxide
  • the precipitate of vial (4) was isolated by filtration and analyzed by NMR, showing that the precipitate was intact pBEBA-2,4-DBP-CHVE polymer (a).
  • the content of vial (5) was analyzed via liquid chromatograph-mass spectrometry (LC-MS), showing that the three main compounds by integration were [1,1′:3′,1′′-terphenyl]-4,4′,4′′-triol (a), benzaldehyde (b) (no mass visible but identity confirmed by NMR), and several isomers of 4′′,5′-bis(4-hydroxyphenyl)-[1,1′:2′,1′′:2′′,1′′′-quaterphenyl]-4,4′,4′′′, 5′′-tetraol (c), which are oxidation products of [1,1′:3′,1′′-terphenyl]-4,4′,4′′-triol.
  • the integral of the LC trace at 250 nm of compounds (a), (

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